Category: Isoxazoles

87988-94-1, 5-Methylisoxazol-4-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,87988-94-1

Example 7 fa) 4-[N-Acetyl-N-(tetrahydro-2H-pyran-4-yl)]amino-5-methylisoxazole; 5-Methyl-4-amino-isoxazole (Reiter, L.A., J. Org. Chem. 1987, 52, 2714-2726) (0.68 g, 5.1 mmol) and acetic acid (0.61 g, 10.2 mmol) were dissolved in MeOH (20 mL). Tetrahydro-2H-pyran-4-one (0.76 g, 7.6 mmol) was added and the mixture was cooled to 0 – (-5) 0C and stirred for 1 h. Sodium cyanoborohydride (0.32 g, 5.1 mmol) was added to the reaction mixture at -5 0C, causing weak exothermic and gas evolution. The cooling bath was removed and the mixture was stirred at r.t. for 1 h, followed by the addition of a second portion of sodium cyanoborohydride (0.1 g, 1.6 mmol). After stirring for 2 h at r.t, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in toluene and re-concentrated. The residue was dissolved in THF (10 mL) and acetic anhydride (1.56 g, 15.3 mmol) was added. The resulting mixture was stirred overnight at r.t. then for 1 h at +50 C. The volatiles were removed in vacuo and the residue was dissolved in toluene and concentrated in vacuo to give the title compound (1.36 g, 78%).1H NMR (CDCl3) ppm delta 8.04 (s, 1 H), 4.86-4.73 (m, 1 H), 4.00-3.89 (m, 2 H), 3.52-3.42 (m, 2 H), 2.35 (s, 3 H), 1.81 (s, 3 H), 1.70-1.57 (m, 2 H), 1.49-1.23 (m, 2 H); MS (ESI) m/z 225 (M+l).; Example 9(a) 5-Acetyl-l-(tetrahydro-2H-pyran-4-yl)- 2-trtfluoromethyl-lH-imidazole; 5-Methyl-4-amino-isoxazole (1.7 g, 17.25 mmol) and acetic acid (1.1 g, 19 mmol) were dissolved in methanol (50 mL). Tetrahydro-2H-pyran-4-one (1.9 g, 19 mmol) was added and the mixture was cooled to 0 – (-5) C and stirred for 1 h. Sodium cyanoborohydride (0.812 g, 12.9 mmol) was added in portions to the reaction mixture at -5 C, causing weak exothermic and gas evolution. The cooling bath was removed and the mixture was stirred at r.t. for 2 h followed by addition of water (20 mL). The methanol was removed from the reaction mixture by vacuum distillation, and the intermediate amine was extracted with ethyl acetate (3×80 mL). The combined organic layers were dried (Na2SO4), concentrated to dryness, dissolved in toluene and re-concentrated. The crude intermediate amine, was dissolved in CH2Cl2 (20 mL) and pyridine (2 mL, 26 mmol) was added. The mixture was cooled to 0C and trifluoroacetic anhydride (4.35 g, 20.7 mmol) was added dropwise. The mixture was continued stirring for 2 h at r.t and was then washed with water and saturated NaHCO3. The aqueous layer was extracted with CH2Cl2 (2×30 mL), the organic extracts were dried (Na2SO4) and concentrated to dryness to give a second crude intermediate, 4- [iV-(tetrahydro-2H-pyran-4-yl)]-iV-trifluoroacetyl-amino-5-methylisoxazole. MS (ES) m/z 279 (M++l). The title compound was prepared in accordance with the general method of Example 6(b) using the intermediate 4-[N-(tetrahydro-2H-pyran-4-yl)]-N-trifluoroacetyl- amino-5-methylisoxazole (max 17.25 mmol), with the exception that the product was purified by flash chromatography (heptane/EtOAc 3:2), giving the title compound (3.03 g,1H NMR (CDCl3, 300 MHz) delta 7.85 (s, 1 H), 4.89-4.75 (m, 1 H), 4.17-4.07 (m, 2 H), 3.54- 3.44 (m, 2 H), 2.75-2.60 (m, 2 H), 2.56 (s, 3 H), 1.72-1.63 (m, 2 H); MS (ES) m/z 263 (M+l).

The synthetic route of 87988-94-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; WO2008/2245; (2008); A2;,
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Isoxazole | C3H3NO – PubChem

1136-45-4, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (l .Og, 4.9mmol, commercially available) and thionyl chloride (5ml) was heated under reflux for 3 h. Removal of excess volatiles by evaporation afforded 5-methyl-3-phenyl-isoxazole-4-carbonyl chloride (1.01 g, 93%) as a yellow oil, which was used without further purification in the next reaction.

1136-45-4, As the paragraph descriping shows that 1136-45-4 is playing an increasingly important role.

Reference£º
Patent; VIRONOVA AB; HOMMAN, Mohammed; KINGI, Ngarita; BERGMAN, Jan; ENGQVIST, Robert; WO2013/171334; (2013); A1;,
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33282-16-5, 5-(4-Methoxyphenyl)isoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of phenylisoxazole acid or phenylpyrazole acid (10a, 10c and 10d) (1 mmol in 30 mL DCM)was added tribromoborane (3 mmol) dropwise under nitrogen at -20C. After the addition, the solution was stirred at room temperature for 24 h. Next, water was added dropwise to this solution until no gas was liberated. The reaction mixture was then extracted with DCM (20 mL ¡Á 2). The organic layer was washed with brine (30 mL ¡Á 2), dried over Na2SO4 and concentrated to obtain a crude demethylated product 10e-g (28% to 49% yields).

33282-16-5, The synthetic route of 33282-16-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wen, Jiachen; Bao, Yu; Niu, Qun; Liu, Jiang; Yang, Jinyu; Wang, Wanqiao; Jiang, Tao; Fan, Yinbo; Li, Kun; Wang, Jian; Zhao, Linxiang; Liu, Dan; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4372 – 4376;,
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Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

a solution of [5-[(3-aminocyclobutyl)methyl]-l,3,4-thiadiazol-2-yl]methanol hydrochloride (500 mg, 2.12 mmol, 1.00 eq., 99%), 5-phenyl-l,2-oxazole-3-carboxylic acid (481 mg, 2.54 mmol, 1.20 eq.), HCTU (1.061 g, 2.55 mmol, 1.20 eq.) and DIEA (1.09 g, 8.43 mmol, 1.20 eq.) in dichloromethane (30 mL) was stirred for 2 hours at room temperature. The resulting mixture was concentrated under vacuum. The crude product was purified by Prep- Flash with acetonitrile and water (0-46% within 40 min). The isomers were separated by Prep- SFC with the following conditions (prep SFC 350-2): Column, Phenomenex Lux 5mu Cellulose- 4, 250*50mm; mobile phase, C02 (50%), MeOH (0.2%DEA) (50%); Detector, UV 220nm. 5-phenyl-iV- [(cis-3- [ [5-(hydroxymethyl)-l,3,4-thiadiazol-2-yl] methyl] cyclobutyl] – 1,2- oxazole-3-carboxamide: [0157] Yield: 37% [0158] Appearance: off-white solid [0159] Analytical data: XH NMR (400MHz, OMSO-d6, ppm): delta: 9.06 (d, J= 8.0Hz, 1H), 7.94-7.92 (m, 2H), 7.58-7.54 (m, 3H), 7.35 (s, 1H), 6.14-6.11 (m, 1H), 4.80 (d, J= 6.0Hz, 2H), 4.35-4.33 (m, 1H), 3.19-3.17 (m, 2H), 2.43-2.33 (m, 3H), 1.99-1.93 (m, 2H). [0160] LC-MS: 371.1 [M+H]+ 5-phenyl-iV- [(trans-3- [ [5-(hydroxymethyl)-l,3,4-thiadiazol-2-yl] methyl] cyclobutyl] – 1,2- oxazole-3-carboxamide: [0161] Yield: 37% [0162] Appearance: light yellow solid [0163] Analytical data: NMR (400MHz, OMSO-d6, ppm): delta: 9.14 (d, J= 7.2Hz, 1H), 7.94-7.92 (m, 2H), 7.56-7.54 (m, 3H), 7.36 (s, 1H), 6.14-6.11 (m, 1H), 4.80 (d, J= 6.0Hz, 2H), 4.63-4.55 (m, 1H), 3.33-3.28 (m, 2H), 2.51-2.49 (m, 1H), 2.33-2.31 (m, 2H) , 2.14-2.13 (m, 2H).

14441-90-8, As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; LEE, Po-shun; (180 pag.)WO2017/40606; (2017); A1;,
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Isoxazole | C3H3NO – PubChem

1083224-23-0, 5-(2,4-Difluorophenyl)isoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of (3S,4S)-4-amino-piperidine-1 ,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (1 g, 3.87 mmol) in DMF (8 mL) at RT is added 5-(2,4-difluorophenyl)isoxazole-3- carboxylic acid (1.3 g, 5.81 mmol). DIPEA (2.12 mL, 12.4 mmol) is then added followed by HATU (1.55 g, 4.06 mmol). The reaction mixture is stirred overnight at RT. The reaction mixture is concentrated, dissolved in DCM (100 mL) and treated twice with aq. sat. NaHC03 (l OOmL). The organic layer is dried over MgS04 and evaporated. The crude residue is purified by flash chromatography over 40 g of silica gel with heptane/EtOAc system (1 :0 to 3:1 )as eluent to yield the title compound as white powder; LC-MS method A: tR = 0.94 min; [M+H]+ = 466.04. 1H NMR (400 MHz, CDCI3) <5: 7.23-7.36 (m, 1 H), 7.96 (m, 1 H), 6.96-7.12 (m, 3 H), 6.79-6.91 (m, 1 H), 4.29-4.51 (m, 2 H), 4.00-4.22 (m, 1 H), 3.64-3.78 (m, 3 H), 2.85- 3.09 (m, 2 H), 2.50-2.68 (m, 1 H), 2.10-2.27 (m, 1 H), 1.42-1.69 (m, 1 1 H), 1.21-1.38 (m, 1 H). 1083224-23-0, 1083224-23-0 5-(2,4-Difluorophenyl)isoxazole-3-carboxylic acid 28951583, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; IDORSIA PHARMACEUTICALS LTD; AISSAOUI, Hamed; GUERRY, Philippe; LEHEMBRE, Francois; POTHIER, Julien; POUZOL, Laetitia; RICHARD-BILDSTEIN, Sylvia; YUAN, Shuguang; (273 pag.)WO2018/19929; (2018); A1;,
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89102-73-8,89102-73-8, Isoxazol-3-ylmethanol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4- [4-(6-Amino-4-methoxypyridin-3-yl)piperidine-l -carbonyl] -3 -fluorophenol (25.0 mg; 0.07 mmol), (l,2-oxazol-3-yl)methanol (6.8 mg; 0.17 mmol), TPP (50.0 mg; 0.19 mmol) and DTAD (40.0 mg; 0.17 mmol) in l,4-dioxane (3 mL) are stirred for 1 hour at 60C. The reaction mixture is purified by RP-HPLC (ACN/water + TFA). Yield: 20.0 mg (39%) ESI-MS: m/z = 427 [M+H]+ Rt(HPLC): 0.52 min (method 11)

89102-73-8 Isoxazol-3-ylmethanol 12905096, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela Kay; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; NETHERTON, Matthew Russell; (119 pag.)WO2019/161010; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33282-23-4,5-(4-Bromophenyl)isoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: To a solution of carboxylic acid 21-29 (1 equiv) in anhydrous CH2Cl2 were successively added HBTU (1.5 equiv), HOBt (0.5 equiv) and DIPEA (2 equiv). The mixture was stirred for 45 min at room temperature. Then, the appropriate amine (1.1 equiv) was introduced and the stirring was continued for 24 h. At the end of the reaction, the mixture was filtered off and the filtrate was successively washed with saturated aqueous NaHCO3 solution, 1N aqueous HCl and distilled water. The organic layer was dried over MgSO4 and was concentrated in vacuo. The resulting residue was purified by TLC (cyclohexane/AcOEt, 7:3) and crystallized in absolute EtOH to give carboxamide 30-48., 33282-23-4

33282-23-4 5-(4-Bromophenyl)isoxazole-3-carboxylic acid 2771350, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Article; Andrzejak, Virginie; Muccioli, Giulio G.; Body-Malapel, Mathilde; El Bakali, Jamal; Djouina, Madjid; Renault, Nicolas; Chavatte, Philippe; Desreumaux, Pierre; Lambert, Didier M.; Millet, Regis; Bioorganic and Medicinal Chemistry; vol. 19; 12; (2011); p. 3777 – 3786;,
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36958-61-9, 5-(Bromomethyl)-3-methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyl-1,2-oxazol-5-yl)propanoate (Racemate) To a solution of 900 mg (2.4 mmol) of tert-butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate in 18 ml of THF under argon at -70 C. were added 3.0 ml (3 0 mmol, 1.25 eq.) of 1 N lithium bis(trimethylsilyl)amide in THF, and the mixture was stirred for 30 min. Subsequently, 623 mg (3.4 mmol, 1.4 eq.) of 5-(bromomethyl)-3-methyl-1,2-oxazole were added, the mixture was stirred at -70 C. for 30 min and then stirred while coming to RT for 90 min. To the reaction mixture were added 15 ml of saturated aqueous ammonium chloride solution, 15 ml of water and 150 ml of ethyl acetate. The aqueous phase was extracted once with ethyl acetate, and the combined organic phases were washed with saturated aqueous sodium chloride solution, then dried and concentrated. The crude product was purified by means of Biotage-Isolera (eluent: cyclohexane/ethyl acetate, 0-38%). Yield: 1.10 g (95% of theory). LC/MS [Method 1]: Rt=1.04 min; MS (ESIpos): m/z=470 (M+H)+, 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=8.03-7.93 (m, 1H), 7.76-7.67 (m, 2H), 7.37 (s, 1H), 6.50 (s, 1H), 6.05 (s, 1H), 5.36 (dd, 1H), 3.72-3.51 (m, 5H), 2.14 (s, 3H), 1.40 (s, 9H), 36958-61-9

As the paragraph descriping shows that 36958-61-9 is playing an increasingly important role.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; STAMPFUss, Jan; (82 pag.)US2017/298052; (2017); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

110256-15-0, 5-Cyclopropylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0285] To a stirred solution of 5-cyclopropylisoxazole-3-carboxylic acid (0.65 g, 1.86 mmol) in DMF (10 mL) was added HATU (1.0 g, 2.8 mmol) and diisopropylethylamine (1.2 ml, 7.44 mmol). The reaction mixture was stirred for 10 min at 0 C and then tert- butyl 4-(amino(3-(methoxycarbonyl)phenyl)methyl)piperidine-l-carboxylate (0.284 g, 1.86 mmol) was added. The reaction mixture was stirred at rt for 2 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2S04 and concentrated under reduced pressure to obtain a crude residue which was purified by column chromatography to afford tert-butyl 4-((5-cyclopropylisoxazole-3-carboxamido)(3-(methoxycarbonyl) phenyl)methyl)piperidine-l-carboxylate (0.789 g, 95 %)., 110256-15-0

110256-15-0 5-Cyclopropylisoxazole-3-carboxylic acid 1092113, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (208 pag.)WO2016/40498; (2016); A1;,
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Isoxazole | C3H3NO – PubChem

53983-15-6, Ethyl 5-amino-4-phenylisoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53983-15-6, EXAMPLE 14 5.0 % (15.1 mmol) of t-butyl [2-(4-phenyl-3-isoxazolecarboxamido)ethyl]carbamate were stirred at room temperature for 16 hours with trifluoroacetic acid analogously to Example 13. After concentration there was obtained a residue which was converted into the hydrochloride. Recrystallization of the crude product from methanol/ether yielded 3.B g (94.1%) of N-(2-aminoethyl)4-phenyl-3-isoxazolecarboxamide hydrochloride as white crystals, melting point 211-212. The t-butyl [2-(4-phenyl-3-isoxazolecarboxamido)ethyl]carbamate used as the starting material was prepared as follows: In an analogous manner to that described in J. Org. Chem. 50 (13) 1985, 2372-2375, 7.6 g (32.72 mmol) of ethyl 5-amino-4-phenyl-3-isoxazolecarboxylate in 160 ml of glacial acetic acid, 50 ml of water and 80 ml of tetrahydrofuran were treated portionwise at 15-20 while stirring within 1 hour with a total of 22.6 g of sodium nitrite. The reaction mixture was thereafter poured into 1 liter of water and extracted 3 times with 400 ml of methylene chloride each time. The organic phases were combined and first washed twice with 1 liter of saturated sodium bicarbonate solution each time and then once with 1 liter of water, dried, filtered and concentrated in a vacuum, whereby after chromatography on silica gel and elution with methylene chloride there were obtained 3.9 g (55%) of ethyl 4-phenyl-3-isoxazolecarboxylate as a yellow oil which was used without further purification.

53983-15-6 Ethyl 5-amino-4-phenylisoxazole-3-carboxylate 4962898, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; Hoffmann-La Roche Inc.; US5011849; (1991); A;,
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